JP2012500500A5 - - Google Patents
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- JP2012500500A5 JP2012500500A5 JP2011523885A JP2011523885A JP2012500500A5 JP 2012500500 A5 JP2012500500 A5 JP 2012500500A5 JP 2011523885 A JP2011523885 A JP 2011523885A JP 2011523885 A JP2011523885 A JP 2011523885A JP 2012500500 A5 JP2012500500 A5 JP 2012500500A5
- Authority
- JP
- Japan
- Prior art keywords
- solvent
- composition
- type material
- active layer
- mpa
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
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- 239000002904 solvent Substances 0.000 claims description 115
- 239000000203 mixture Substances 0.000 claims description 85
- CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 claims description 58
- 239000000463 material Substances 0.000 claims description 38
- 238000000034 method Methods 0.000 claims description 38
- 150000001875 compounds Chemical class 0.000 claims description 25
- RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 claims description 22
- OSWPMRLSEDHDFF-UHFFFAOYSA-N methyl salicylate Chemical compound COC(=O)C1=CC=CC=C1O OSWPMRLSEDHDFF-UHFFFAOYSA-N 0.000 claims description 22
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 21
- SMQUZDBALVYZAC-UHFFFAOYSA-N salicylaldehyde Chemical compound OC1=CC=CC=C1C=O SMQUZDBALVYZAC-UHFFFAOYSA-N 0.000 claims description 18
- 150000004996 alkyl benzenes Chemical class 0.000 claims description 16
- 230000003746 surface roughness Effects 0.000 claims description 15
- PKZJLOCLABXVMC-UHFFFAOYSA-N 2-Methoxybenzaldehyde Chemical compound COC1=CC=CC=C1C=O PKZJLOCLABXVMC-UHFFFAOYSA-N 0.000 claims description 14
- XMWRBQBLMFGWIX-UHFFFAOYSA-N C60 fullerene Chemical class C12=C3C(C4=C56)=C7C8=C5C5=C9C%10=C6C6=C4C1=C1C4=C6C6=C%10C%10=C9C9=C%11C5=C8C5=C8C7=C3C3=C7C2=C1C1=C2C4=C6C4=C%10C6=C9C9=C%11C5=C5C8=C3C3=C7C1=C1C2=C4C6=C2C9=C5C3=C12 XMWRBQBLMFGWIX-UHFFFAOYSA-N 0.000 claims description 14
- RGSFGYAAUTVSQA-UHFFFAOYSA-N Cyclopentane Chemical compound C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 claims description 14
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical group CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims description 14
- URLKBWYHVLBVBO-UHFFFAOYSA-N Para-Xylene Chemical group CC1=CC=C(C)C=C1 URLKBWYHVLBVBO-UHFFFAOYSA-N 0.000 claims description 14
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 claims description 14
- BGTOWKSIORTVQH-UHFFFAOYSA-N cyclopentanone Chemical compound O=C1CCCC1 BGTOWKSIORTVQH-UHFFFAOYSA-N 0.000 claims description 14
- IVSZLXZYQVIEFR-UHFFFAOYSA-N m-xylene Chemical group CC1=CC=CC(C)=C1 IVSZLXZYQVIEFR-UHFFFAOYSA-N 0.000 claims description 14
- QPJVMBTYPHYUOC-UHFFFAOYSA-N methyl benzoate Chemical compound COC(=O)C1=CC=CC=C1 QPJVMBTYPHYUOC-UHFFFAOYSA-N 0.000 claims description 14
- ZRSNZINYAWTAHE-UHFFFAOYSA-N p-methoxybenzaldehyde Chemical compound COC1=CC=C(C=O)C=C1 ZRSNZINYAWTAHE-UHFFFAOYSA-N 0.000 claims description 14
- UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 claims description 11
- 229960001047 methyl salicylate Drugs 0.000 claims description 11
- 150000001717 carbocyclic compounds Chemical class 0.000 claims description 8
- 229910003472 fullerene Inorganic materials 0.000 claims description 8
- DMEGYFMYUHOHGS-UHFFFAOYSA-N heptamethylene Natural products C1CCCCCC1 DMEGYFMYUHOHGS-UHFFFAOYSA-N 0.000 claims description 7
- AUHZEENZYGFFBQ-UHFFFAOYSA-N mesitylene Substances CC1=CC(C)=CC(C)=C1 AUHZEENZYGFFBQ-UHFFFAOYSA-N 0.000 claims description 7
- 125000001827 mesitylenyl group Chemical group [H]C1=C(C(*)=C(C([H])=C1C([H])([H])[H])C([H])([H])[H])C([H])([H])[H] 0.000 claims description 7
- 229940095102 methyl benzoate Drugs 0.000 claims description 7
- 229940078552 o-xylene Drugs 0.000 claims description 7
- YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Natural products C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 claims description 4
- 238000000137 annealing Methods 0.000 claims description 4
- 125000002837 carbocyclic group Chemical group 0.000 claims description 4
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 4
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 4
- 125000000623 heterocyclic group Chemical group 0.000 claims description 4
- 150000002469 indenes Chemical class 0.000 claims description 4
- 125000001624 naphthyl group Chemical group 0.000 claims description 4
- 150000002894 organic compounds Chemical class 0.000 claims description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
- 125000004076 pyridyl group Chemical group 0.000 claims description 4
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims description 4
- 150000003839 salts Chemical class 0.000 claims description 4
- 239000012453 solvate Substances 0.000 claims description 4
- 239000006185 dispersion Substances 0.000 claims description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims description 3
- 239000001257 hydrogen Substances 0.000 claims description 3
- 229920000547 conjugated polymer Polymers 0.000 claims description 2
- -1 as engineering Chemical class 0.000 claims 2
- 229920000123 polythiophene Polymers 0.000 description 2
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US9046408P | 2008-08-20 | 2008-08-20 | |
| US61/090,464 | 2008-08-20 | ||
| PCT/US2009/053833 WO2010021921A1 (en) | 2008-08-20 | 2009-08-14 | Improved solvent system for fabrication of organic solar cells |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2012500500A JP2012500500A (ja) | 2012-01-05 |
| JP2012500500A5 true JP2012500500A5 (enExample) | 2012-09-20 |
Family
ID=41172441
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2011523885A Withdrawn JP2012500500A (ja) | 2008-08-20 | 2009-08-14 | 有機太陽電池の製造のための改善された溶媒システム |
Country Status (5)
| Country | Link |
|---|---|
| US (1) | US20100043876A1 (enExample) |
| EP (1) | EP2327116A1 (enExample) |
| JP (1) | JP2012500500A (enExample) |
| KR (1) | KR20110058808A (enExample) |
| WO (1) | WO2010021921A1 (enExample) |
Families Citing this family (48)
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|---|---|---|---|---|
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| US8691931B2 (en) * | 2009-09-04 | 2014-04-08 | Plextronics, Inc. | Organic electronic devices and polymers, including photovoltaic cells and diketone-based and diketopyrrolopyrrole-based polymers |
| US20140147996A1 (en) * | 2010-11-29 | 2014-05-29 | Arizon Board of Regents Acting for and on Behalf Arizona State University | Methods for fabricating bulk heterojunctions using solution processing techniques |
| WO2012102066A1 (ja) | 2011-01-25 | 2012-08-02 | コニカミノルタホールディングス株式会社 | 有機光電変換層材料組成物、有機光電変換素子、有機光電変換素子の製造方法及び太陽電池 |
| TW201238994A (en) * | 2011-02-14 | 2012-10-01 | Sumitomo Chemical Co | Method for producing photoelectric transducering element |
| TW201307427A (zh) * | 2011-02-14 | 2013-02-16 | Sumitomo Chemical Co | 有機光電變換元件的製造方法 |
| EP2544256A1 (en) | 2011-07-04 | 2013-01-09 | LANXESS Deutschland GmbH | Two-component electron-selective buffer layer and photovoltaic cells using the same |
| KR101936978B1 (ko) | 2011-07-05 | 2019-01-09 | 닛산 가가쿠 가부시키가이샤 | 수직 상-분리 반도체 유기 물질 층 |
| JP6265897B2 (ja) | 2011-08-26 | 2018-01-24 | メルク パテント ゲゼルシャフト ミット ベシュレンクテル ハフツングＭｅｒｃｋ Ｐａｔｅｎｔ Ｇｅｓｅｌｌｓｃｈａｆｔ ｍｉｔ ｂｅｓｃｈｒａｅｎｋｔｅｒ Ｈａｆｔｕｎｇ | 有機半導体配合物 |
| EP2764518A1 (en) | 2011-10-04 | 2014-08-13 | Plextronics, Inc. | Improved doping methods for hole injection and transport layers |
| JP5915969B2 (ja) * | 2012-03-09 | 2016-05-11 | 三菱化学株式会社 | 光電変換素子及び太陽電池モジュール |
| GB201210858D0 (en) * | 2012-06-19 | 2012-08-01 | Cambridge Display Tech Ltd | Method |
| US9293711B2 (en) | 2012-08-09 | 2016-03-22 | Polyera Corporation | Organic semiconductor formulations |
| EP2698834A1 (en) | 2012-08-17 | 2014-02-19 | LANXESS Deutschland GmbH | Fullerene derivatives with reduced electron affinity and a photovoltaic cell using the same |
| WO2014031977A1 (en) | 2012-08-24 | 2014-02-27 | Arizona Board Of Regents For And On Behalf Of Arizona State University | Metal compounds and methods and uses thereof |
| US9882150B2 (en) | 2012-09-24 | 2018-01-30 | Arizona Board Of Regents For And On Behalf Of Arizona State University | Metal compounds, methods, and uses thereof |
| WO2014109814A2 (en) | 2012-10-26 | 2014-07-17 | Arizona Board Of Regents Acting For And On Behalf Of Arizona State University | Metal complexes, methods, and uses thereof |
| JP6804823B2 (ja) | 2013-10-14 | 2020-12-23 | アリゾナ・ボード・オブ・リージェンツ・オン・ビハーフ・オブ・アリゾナ・ステイト・ユニバーシティーＡｒｉｚｏｎａ Ｂｏａｒｄ ｏｆ Ｒｅｇｅｎｔｓ ｏｎ ｂｅｈａｌｆ ｏｆ Ａｒｉｚｏｎａ Ｓｔａｔｅ Ｕｎｉｖｅｒｓｉｔｙ | 白金錯体およびデバイス |
| US10020455B2 (en) | 2014-01-07 | 2018-07-10 | Arizona Board Of Regents On Behalf Of Arizona State University | Tetradentate platinum and palladium complex emitters containing phenyl-pyrazole and its analogues |
| US9941479B2 (en) | 2014-06-02 | 2018-04-10 | Arizona Board Of Regents On Behalf Of Arizona State University | Tetradentate cyclometalated platinum complexes containing 9,10-dihydroacridine and its analogues |
| US9923155B2 (en) | 2014-07-24 | 2018-03-20 | Arizona Board Of Regents On Behalf Of Arizona State University | Tetradentate platinum (II) complexes cyclometalated with functionalized phenyl carbene ligands and their analogues |
| WO2016025921A1 (en) | 2014-08-15 | 2016-02-18 | Arizona Board Of Regents On Behalf Of Arizona State University | Non-platinum metal complexes for excimer based single dopant white organic light emitting diodes |
| US11329244B2 (en) | 2014-08-22 | 2022-05-10 | Arizona Board Of Regents On Behalf Of Arizona State University | Organic light-emitting diodes with fluorescent and phosphorescent emitters |
| WO2016052254A1 (ja) * | 2014-09-30 | 2016-04-07 | 富士フイルム株式会社 | 有機半導体膜形成用組成物、並びに、有機半導体素子及びその製造方法 |
| KR101687807B1 (ko) | 2014-10-27 | 2017-01-02 | 주식회사 엘지화학 | 유기 태양전지용 잉크 조성물 및 이를 이용한 유기 태양전지 제조방법 |
| US10033003B2 (en) | 2014-11-10 | 2018-07-24 | Arizona Board Of Regents On Behalf Of Arizona State University | Tetradentate metal complexes with carbon group bridging ligands |
| JP6159034B2 (ja) * | 2014-11-13 | 2017-07-05 | 住友化学株式会社 | インク組成物およびそれを用いて製造した光電変換素子 |
| US9879039B2 (en) | 2015-06-03 | 2018-01-30 | Arizona Board Of Regents On Behalf Of Arizona State University | Tetradentate and octahedral metal complexes containing naphthyridinocarbazole and its analogues |
| JP6661365B2 (ja) * | 2015-12-17 | 2020-03-11 | 東芝テック株式会社 | インクジェットインク並びに有機薄膜太陽電池の製造方法及び製造装置 |
| US11335865B2 (en) | 2016-04-15 | 2022-05-17 | Arizona Board Of Regents On Behalf Of Arizona State University | OLED with multi-emissive material layer |
| KR102888327B1 (ko) | 2016-10-12 | 2025-11-18 | 아리조나 보드 오브 리젠츠 온 비하프 오브 아리조나 스테이트 유니버시티 | 협대역 적색 인광성 4좌 백금(ii) 착물 |
| US11183670B2 (en) | 2016-12-16 | 2021-11-23 | Arizona Board Of Regents On Behalf Of Arizona State University | Organic light emitting diode with split emissive layer |
| WO2018140765A1 (en) | 2017-01-27 | 2018-08-02 | Jian Li | Metal-assisted delayed fluorescent emitters employing pyrido-pyrrolo-acridine and analogues |
| US10516117B2 (en) | 2017-05-19 | 2019-12-24 | Arizona Board Of Regents On Behalf Of Arizona State University | Metal-assisted delayed fluorescent emttters employing benzo-imidazo-phenanthridine and analogues |
| US11101435B2 (en) | 2017-05-19 | 2021-08-24 | Arizona Board Of Regents On Behalf Of Arizona State University | Tetradentate platinum and palladium complexes based on biscarbazole and analogues |
| JP6390773B2 (ja) * | 2017-09-12 | 2018-09-19 | 三菱ケミカル株式会社 | 有機薄膜太陽電池素子の製造方法 |
| US11647643B2 (en) | 2017-10-17 | 2023-05-09 | Arizona Board Of Regents On Behalf Of Arizona State University | Hole-blocking materials for organic light emitting diodes |
| WO2019079508A2 (en) | 2017-10-17 | 2019-04-25 | Jian Li | PREFERRED MOLECULAR ORIENTATED PHOSPHORESCENT EXCIMERS AS MONOCHROMATIC TRANSMITTERS FOR DISPLAY AND LIGHTING APPLICATIONS |
| US12037348B2 (en) | 2018-03-09 | 2024-07-16 | Arizona Board Of Regents On Behalf Of Arizona State University | Blue and narrow band green and red emitting metal complexes |
| US11878988B2 (en) | 2019-01-24 | 2024-01-23 | Arizona Board Of Regents On Behalf Of Arizona State University | Blue phosphorescent emitters employing functionalized imidazophenthridine and analogues |
| US11594691B2 (en) | 2019-01-25 | 2023-02-28 | Arizona Board Of Regents On Behalf Of Arizona State University | Light outcoupling efficiency of phosphorescent OLEDs by mixing horizontally aligned fluorescent emitters |
| US12245492B2 (en) * | 2019-03-28 | 2025-03-04 | Raynergy Tek Incorporation | Organic semiconductor formulation |
| US11785838B2 (en) | 2019-10-02 | 2023-10-10 | Arizona Board Of Regents On Behalf Of Arizona State University | Green and red organic light-emitting diodes employing excimer emitters |
| CN113683625B (zh) | 2020-05-19 | 2025-06-10 | 亚利桑那州立大学董事会 | 用于有机发光二极管的金属辅助延迟荧光发射体 |
| US11945985B2 (en) | 2020-05-19 | 2024-04-02 | Arizona Board Of Regents On Behalf Of Arizona State University | Metal assisted delayed fluorescent emitters for organic light-emitting diodes |
| JP2023107154A (ja) * | 2022-01-21 | 2023-08-02 | 住友化学株式会社 | インク組成物及び当該インク組成物を用いた光電変換素子 |
| KR102637059B1 (ko) * | 2022-01-28 | 2024-02-16 | 한국과학기술연구원 | 수분차단막을 이용한 화합물의 형성방법, 및 이를 이용한 칼코파이라이트 화합물 박막과 태양전지의 제조방법 |
Family Cites Families (19)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE4110263A1 (de) * | 1991-03-28 | 1992-10-01 | Hoechst Ag | Waessrige dispersion aus intrinsisch elektrisch leitfaehigen polyalkoxythiophenen, verfahren zu ihrer herstellung und ihre verwendung |
| US5331183A (en) * | 1992-08-17 | 1994-07-19 | The Regents Of The University Of California | Conjugated polymer - acceptor heterojunctions; diodes, photodiodes, and photovoltaic cells |
| US6166172A (en) * | 1999-02-10 | 2000-12-26 | Carnegie Mellon University | Method of forming poly-(3-substituted) thiophenes |
| US6454880B1 (en) * | 1999-09-29 | 2002-09-24 | Herbert (Lonny) A. Rickman, Jr. | Material for die casting tooling components, method for making same, and tooling components made from the material and process |
| KR20080110928A (ko) * | 2001-03-10 | 2008-12-19 | 메르크 파텐트 게엠베하 | 유기 반도체 용액 및 분산액 |
| US6602974B1 (en) * | 2001-12-04 | 2003-08-05 | Carnegie Mellon University | Polythiophenes, block copolymers made therefrom, and methods of forming the same |
| US7147936B2 (en) * | 2002-08-23 | 2006-12-12 | Agfa Gevaert | Layer configuration with improved stability to sunlight exposure |
| EP1566845A4 (en) * | 2002-11-28 | 2009-08-12 | Nippon Oil Corp | PHOTOELECTRIC CONVERSION ELEMENT |
| DE102004007777A1 (de) * | 2004-02-18 | 2005-09-08 | Covion Organic Semiconductors Gmbh | Lösungen organischer Halbleiter |
| DE102004023276A1 (de) * | 2004-05-11 | 2005-12-01 | Covion Organic Semiconductors Gmbh | Lösungen organischer Halbleiter |
| KR20070102661A (ko) * | 2004-09-24 | 2007-10-19 | 플렉스트로닉스, 인크 | 광기전 전지에서의 헤테로 원자를 갖는 위치 규칙적폴리(3-치환 티오펜) |
| WO2006086480A2 (en) * | 2005-02-10 | 2006-08-17 | Plextronics, Inc. | Hole injection/transport layer compositions and devices |
| WO2006101953A2 (en) * | 2005-03-16 | 2006-09-28 | Plextronics, Inc. | Copolymers of soluble poly (thiophenes) with improved electronic performance |
| JP5193851B2 (ja) * | 2005-04-01 | 2013-05-08 | カーネギー メロン ユニバーシティ | レジオレギュラーポリマー、ポリチオフェンおよびブロックコポリマーを含む導電性ポリマーのリビング合成法 |
| US9136489B2 (en) * | 2006-05-02 | 2015-09-15 | Mitsubishi Chemical Corporation | Method for producing organic photoelectric conversion device and organic photoelectric conversion device |
| WO2008066933A2 (en) * | 2006-12-01 | 2008-06-05 | The Regents Of The University Of California | Enhancing performance characteristics of organic semiconducting films by improved solution processing |
| US20080299293A1 (en) * | 2007-05-02 | 2008-12-04 | Plextronics, Inc. | Solvent system for conjugated polymers |
| US8227691B2 (en) * | 2007-10-31 | 2012-07-24 | The Regents Of The University Of California | Processing additives for fabricating organic photovoltaic cells |
| KR101683026B1 (ko) * | 2008-04-11 | 2016-12-07 | 닛산 가가쿠 고교 가부시키 가이샤 | 도핑된 공액 중합체, 소자, 및 소자의 제조 방법 |
-
2009
- 2009-08-14 US US12/541,500 patent/US20100043876A1/en not_active Abandoned
- 2009-08-14 EP EP09791523A patent/EP2327116A1/en not_active Withdrawn
- 2009-08-14 KR KR1020117005618A patent/KR20110058808A/ko not_active Ceased
- 2009-08-14 JP JP2011523885A patent/JP2012500500A/ja not_active Withdrawn
- 2009-08-14 WO PCT/US2009/053833 patent/WO2010021921A1/en not_active Ceased
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